WO1998000392A1 - Procede de preparation d'alcoxylates de monoamides, de diamides ou d'oligoamides - Google Patents

Procede de preparation d'alcoxylates de monoamides, de diamides ou d'oligoamides Download PDF

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Publication number
WO1998000392A1
WO1998000392A1 PCT/EP1996/003776 EP9603776W WO9800392A1 WO 1998000392 A1 WO1998000392 A1 WO 1998000392A1 EP 9603776 W EP9603776 W EP 9603776W WO 9800392 A1 WO9800392 A1 WO 9800392A1
Authority
WO
WIPO (PCT)
Prior art keywords
catalyst
amidation
carboxylic acid
alkoxylates
alkoxylation
Prior art date
Application number
PCT/EP1996/003776
Other languages
German (de)
English (en)
Inventor
Ulrike Jacobs
Uwe Kaltwasser
Klaus Kwetkat
Ernst-Jürgen LEHMANN
Original Assignee
Rwe-Dea Aktiengesellschaft Für Mineraloel Und Chem
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Rwe-Dea Aktiengesellschaft Für Mineraloel Und Chem filed Critical Rwe-Dea Aktiengesellschaft Für Mineraloel Und Chem
Priority to JP10503771A priority Critical patent/JP2001502295A/ja
Priority to US09/214,052 priority patent/US6211409B1/en
Priority to AU69847/96A priority patent/AU726173B2/en
Priority to AT96930969T priority patent/ATE288416T1/de
Priority to EP96930969A priority patent/EP0912497B1/fr
Priority to DE59611190T priority patent/DE59611190D1/de
Publication of WO1998000392A1 publication Critical patent/WO1998000392A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/526—Carboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 are polyalkoxylated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/08—Preparation of carboxylic acid amides from amides by reaction at nitrogen atoms of carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/14—Preparation of carboxylic acid amides by formation of carboxamide groups together with reactions not involving the carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
    • C07C233/35—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/36—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton

Definitions

  • WO 95/19955 deals in one example with the manufacture of the structure described in detail, this description also being said to apply analogously to other claimed structures.
  • the A used should first be reacted with one mole of ethylene oxide per primary or secondary amino group in the molecule, then the secondary and ⁇ -amino groups should be acylated with carboxylic acid methyl ester and then in a third step with the rest for the End product necessary alkoxy units to be implemented.
  • the invention thus relates to a process for the preparation of mono-, di- or oligo-idalk-oxylates, characterized in that diamides are prepared from carboxylic acids or carboxylic acid alkyl esters and di-, oligo- or polyamines and directly after their preparation, without interim Isolation or workup, alkoxylated as a melt. If free carboxylic acids are used, the catalyst can be dispensed with. In this case, the alkoxylation catalyst is metered in after the amidation has ended.
  • the reactions can be carried out as a one-pot reaction or alternatively in two different reactors.
  • the reactors should then advantageously not be spatially far apart, but even a greater spatial distance when using heated lines is not a fundamental obstacle to the process according to the invention.
  • the process is characterized in that carboxylic acids or carboxylic acid methyl esters with 4 to 24, preferably 8 to 18, carbon atoms in the underlying carboxylic acid and mixtures thereof are introduced together, and the di-oligo- or polyamine is then mixed in.
  • the carbon chain of the carboxylic acids or carboxylic acid methyl esters can be branched or unbranched, cyclic or acyclic, aliphatic or aromatic.
  • Suitable di-, oligo- or polyamines for the process according to the invention are all amines described both in DE 44 40 328 and in WO 95/19955. The only requirement for the mixture is that the components are filled into a suitable reactor in the liquid state. All steps are done with a nitrogen blanket.
  • catalysts for the amidation are suitable as catalysts, such as.
  • potassium or sodium methoxide, potassium or sodium ethanolate, potassium hydroxide, sodium hydroxide, tin oxalate, elemental tin, zinc oxide and potassium tert-butoxide, sodium and potassium alcoholates and hydroxides are particularly preferred.
  • the catalyst is used in concentrations of 0 to 5% by weight, preferably 0 to 3 and particularly preferably 0 to 1% by weight, based on the total batch (for the amidation).
  • the internal temperature of the reactor is increased to at least 2 to 5 ° C. above the solidification temperature of the product slide and to a maximum of 240 ° C., preferably to 80 to 200 ° C. and particularly preferably to 100 to 190 ° C.
  • the removal of water or methanol, depending on the starting material is started immediately or the process is continued until a constant bottom and top temperature has been set, that is to say the reaction equilibrium has been set.
  • the temperatures required for this depend on the specific raw material mixture and are in the above range.
  • the necessary times are in the range from 10 to 120, preferably 15 to 60 and particularly preferably 15 to 40 minutes.
  • the temperature is set as far as possible (2 to 5 ° C. above the solidification point of the product amide), but not below 90, preferably 130 to 180 ° C.
  • catalyst can be added.
  • the catalysts which can be used are all catalysts which are suitable for alkoxylations, including those which lead to narrow homolog distributions. Examples include sodium and potassium alkoxylates and hydroxides, layered silicates and hydrotalcite. Sodium and potassium alkoxylates and hydroxides are preferred.
  • the alkoxylation is carried out with the necessary amount of alkylene oxide according to the prior art at 2 to 6 bar total pressure and 100 to 190 ° C., preferably 130 to 185 ° C.
  • the product is discharged at 40 to 160 ° C, preferably 45 to 120 ° C.
  • the catalyst e.g. B. neutralized with low molecular weight carboxylic acids such as lactic acid. Filtration follows when heterogeneous catalysts are used. If the alkoxylate is used as the end product, if necessary, e.g. B. be bleached with hydrogen peroxide.
  • the neutralization can optionally be dispensed with and the sulfonation with an S0 / air mixture or oleum or chlorosulfonic acid or A idosulfonic acid, but preferably with an S0 3 / air mixture, carried out directly afterwards become.
  • This is followed by neutralization with corresponding equivalents of alkali or alkaline earth metal hydroxides or with corresponding equivalents of mono-, di- and trialchanols. Thanks to the gentle production of the preliminary stages, products of high color quality of the desired structure can also be produced after this step.
  • bleaching e.g. B. with hydrogen peroxide, connect.
  • the process according to the invention is characterized in that it allows the structures described in DE 44 40 328 or WO 95/19955 to be purified in high purity with more than 70 mol%, preferably more than 80 mol% and particularly preferably more than 85 Mol to produce and thus to come to more efficient, that is also cheaper surfactants or formulations.
  • the fatty acid methyl ester and the amine were combined in a suitable reactor with a volume of 1,000 liters and the catalyst was then added. The mixture was heated to reflux, which started at a bottom temperature of about 120 ° C. When the reaction equilibrium occurred after about 40 minutes, a bottom temperature of about 106 ° C. and a top temperature of 70 ° C. were established. The methanol formed was distilled off and the bottom temperature was raised to 180.degree.
  • reaction was continued immediately.
  • a reaction temperature of 165 ° C 0.5 bar of nitrogen were injected and supplemented with E0 to 3.0 bar, where this pressure was maintained by continuously supplying the EO.
  • the intended amount of EO was taken up after about 1.5 hours.
  • residues of EO contained were blown out with nitrogen and the reaction product was then discharged with a nitrogen purge.
  • the product is light, iodine color number of 28, and corresponds to the required structure according to 13 C NMR.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Detergent Compositions (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

L'invention concerne un procédé de préparation d'alcoxylates de monoamides, de diamides ou d'oligoamides. On prépare des diamides à partir d'acides carboxyliques ou d'esters d'alkyle d'acide carboxylique et de diamines, d'oligoamines ou de polyamines et on les alcoxyle sous forme d'une masse fondue directement après leur préparation, sans traitements intermédiaires.
PCT/EP1996/003776 1996-06-28 1996-08-28 Procede de preparation d'alcoxylates de monoamides, de diamides ou d'oligoamides WO1998000392A1 (fr)

Priority Applications (6)

Application Number Priority Date Filing Date Title
JP10503771A JP2001502295A (ja) 1996-06-28 1996-08-28 ジ―、またはオリゴアミドアルコキシレートを調製する方法
US09/214,052 US6211409B1 (en) 1996-06-28 1996-08-28 Process for preparing mono-, Di- or oligoamide alkoxylates
AU69847/96A AU726173B2 (en) 1996-06-28 1996-08-28 Process for preparing di- or oligoamide alkoxylates
AT96930969T ATE288416T1 (de) 1996-06-28 1996-08-28 Verfahren zur herstellung von di- oder oligoamidalkoxylaten
EP96930969A EP0912497B1 (fr) 1996-06-28 1996-08-28 Procede de preparation d'alcoxylates de diamides ou d'oligoamides
DE59611190T DE59611190D1 (de) 1996-06-28 1996-08-28 Verfahren zur herstellung von di- oder oligoamidalkoxylaten

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19625937.1 1996-06-28
DE19625937A DE19625937A1 (de) 1996-06-28 1996-06-28 Verfahren zur Herstellung von Mono-, Di- oder Oligoamidalkoxylaten

Publications (1)

Publication Number Publication Date
WO1998000392A1 true WO1998000392A1 (fr) 1998-01-08

Family

ID=7798288

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1996/003776 WO1998000392A1 (fr) 1996-06-28 1996-08-28 Procede de preparation d'alcoxylates de monoamides, de diamides ou d'oligoamides

Country Status (8)

Country Link
US (1) US6211409B1 (fr)
EP (1) EP0912497B1 (fr)
JP (1) JP2001502295A (fr)
AT (1) ATE288416T1 (fr)
AU (1) AU726173B2 (fr)
DE (2) DE19625937A1 (fr)
ES (1) ES2236750T3 (fr)
WO (1) WO1998000392A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2235134A1 (fr) * 2007-12-21 2010-10-06 Huntsman Petrochemical LLC Procédé de préparation d'alcoxylates d'amidoamine et leurs compositions

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB835566A (en) * 1956-11-23 1960-05-25 Ici Ltd Improvements in or relating to the spinning of rayon from viscose
EP0038862A1 (fr) * 1979-08-03 1981-11-04 Albright & Wilson Limited Compositions contenant les sels d'amidoamines et leur utilisation comme agents adoucissants pour matières textiles
GB2203177A (en) * 1987-04-04 1988-10-12 Sandoz Ltd Softener compositions containing acylated polyamines
DE4440328A1 (de) * 1994-11-11 1996-05-15 Huels Chemische Werke Ag Amphiphile Verbindungen mit mindestens zwei hydrophilen und mindestens zwei hydrophoben Gruppen auf der Basis von Amiden

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995019955A1 (fr) 1994-01-25 1995-07-27 The Procter & Gamble Company Amides jumeles de polyether d'acides gras

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB835566A (en) * 1956-11-23 1960-05-25 Ici Ltd Improvements in or relating to the spinning of rayon from viscose
EP0038862A1 (fr) * 1979-08-03 1981-11-04 Albright & Wilson Limited Compositions contenant les sels d'amidoamines et leur utilisation comme agents adoucissants pour matières textiles
GB2203177A (en) * 1987-04-04 1988-10-12 Sandoz Ltd Softener compositions containing acylated polyamines
DE4440328A1 (de) * 1994-11-11 1996-05-15 Huels Chemische Werke Ag Amphiphile Verbindungen mit mindestens zwei hydrophilen und mindestens zwei hydrophoben Gruppen auf der Basis von Amiden

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2235134A1 (fr) * 2007-12-21 2010-10-06 Huntsman Petrochemical LLC Procédé de préparation d'alcoxylates d'amidoamine et leurs compositions
EP2235134A4 (fr) * 2007-12-21 2015-04-08 Huntsman Petrochemical Llc Procédé de préparation d'alcoxylates d'amidoamine et leurs compositions

Also Published As

Publication number Publication date
ES2236750T3 (es) 2005-07-16
EP0912497A1 (fr) 1999-05-06
ATE288416T1 (de) 2005-02-15
EP0912497B1 (fr) 2005-02-02
JP2001502295A (ja) 2001-02-20
AU6984796A (en) 1998-01-21
AU726173B2 (en) 2000-11-02
US6211409B1 (en) 2001-04-03
DE59611190D1 (de) 2005-03-10
DE19625937A1 (de) 1997-01-23

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